MAJOR Issues with iPod and iTUNES

My godbrother has had some major issues with his ipod video ever since his computer got screwed up when it was disconnected during some construction a few weeks back. For some reason all of the videos and songs he purchased off of iTUNES were not playing properly. So, I went online and reset his ipod, but that wasn't making a difference. After I did that, I tried to connect his ipod to his comp and his icon didnt appear in iTUNES. This also happened to me and so I did what was recommended to me when I had problems with my nano and re-uploaded his itunes. But for some reason his new version of itunes doesn't recognize his old library, and keeps sending up these errors that the library was made in a newer version of itunes, but the only problem is he uploaded the newest version of itunes off of the apple website.

This is a long shot but does anyone have a clue as to what should be done?